Material for organic electroluminescent device and organic electroluminescent device using same

ABSTRACT

The present invention provides a material for an organic electroluminescence device having a specific structure in which a dibennzofuranyl group or a dibenzothiophenyl group is bonded at an N-position (9-position) of a carbazolyl group and an organic electroluminescence device which is provided with one or more organic thin film layers including a light emitting layer between a cathode and an anode and in which at least one layer of the organic thin film layers described above contains the material for an organic electroluminescence device according to the present invention.

BACKGROUND OF THE INVENTION

1. Technical Field

The present invention relates to a material for an organicelectroluminescence device and an organic electroluminescence deviceprepared by using the same.

2. Background Art

An organic electroluminescence device (hereinafter “electroluminescence”shall be abbreviated as EL) is a spontaneous light emitting devicemaking use of the principle that a fluorescent substance or aphosphorescent substance emits light by recombination energy of holesinjected from an anode and electrons injected from a cathode by applyingan electric field. Since a laminate type organic EL device operated at alow voltage was reported, researches on organic EL devices comprisingorganic materials as structural materials have actively been carriedout. In the above laminate type device, tris(8-quinolinolate)aluminum isused for the light emitting layer, and a tetraphenyldiamine derivativeis used for the hole transporting layer. The advantages of the laminatestructure include an elevation in an efficiency of injecting holes intoa light emitting layer, a rise in a production efficiency of excitonsproduced by blocking electrons injected from a cathode to recombine themand shutting up of excitons produced in a light emitting layer. As shownin the above example, a two-layer type comprising a hole transporting(injecting) layer and an electron transporting and light emitting layerand a three-layer type comprising a hole transporting (injecting) layer,a light emitting layer and an electron transporting (injecting) layerare well known as the device structures of an organic EL device. In theabove laminate type structural devices, device structures and formingmethods are studied in order to enhance a recombination efficiency ofholes and electrons injected.

Known as light emitting materials for an organic EL device are lightemitting materials such as chelate complexes such as atris(8-quinolinolate)aluminum complex and the like, coumarinderivatives, tetraphenylbutadiene derivatives, distyrylarylenederivatives, oxadiazole derivatives and the like. It is reported thatlight emission of a blue color to a red color in a visible region isobtained from the above light emitting materials, and color displaydevices are materialized.

Fluorescent materials which emit light by a singlet exciton have so farbeen used as light emitting materials for an organic EL device. Inrecent years, it is proposed to make use of phosphorescence luminescencematerials which emit light by a triplet exciton in addition tofluorescent materials (for example, non-patent documents 1 and 2). It isconsidered that when an electron is recombined with a hole in an organicEL device, singlet excitons and triplet excitons are formed in aproportion of 1:3 due to a difference thereof in a spin multiplicity,and therefore an organic EL device prepared by using a phosphorescenceluminescence material can achieve a luminous efficiency which is largerby three to four times as compared with that of an organic EL deviceprepared by using only a fluorescent material. In blue colorphosphorescent emission, however, it is difficult to achieve the highefficiency and the long lifetime, and a host material which achievesthem is desired to be developed.

A compound to which two carbazole skeletons are bonded via linkagegroups is proposed in a patent document 1. A compound in which twocarbazole skeletons are bonded to one dibenzofuran skeleton ordibenzothiophene skeleton is proposed in a patent document 2 (forexample, compounds 23 and 24). A compound in which two carbazoleskeletons are bonded to one dibenzofuran skeleton is proposed in apatent document 3 (for example, compound 43).

However, compounds which have two carbazole skeletons and to which adibenzofuran skeleton or a dibenzothiophene skeleton is bonded at sitesof N in the respective skeletons, if necessary, via linkage groups arenot described in the above documents.

Further, the compounds described in the patent documents 1 to 3 wereunsatisfactory in an efficiency and a lifetime in blue colorphosphorescent emission.

-   Patent document 1: WO2007/108459-   Patent document 2: WO2007/119816-   Patent document 3: WO2007/077810-   Non-patent document 1: Applied Physics Letters Vol. 74, No. 3, pp.    442 to 444-   Non-patent document 2: Applied Physics Letters Vol. 75, No. 1, pp. 4    to 6

SUMMARY OF THE INVENTION Problems to be Solved by the Invention

The present invention has been made in order to solve the problemsdescribed above, and an object of the present invention is to provide anorganic EL device having a high efficiency and a long lifetime inphosphorescent emission and a material for an organic EL device whichmaterializes the same.

Means for Solving the Problems

Intense researches repeated by the present inventors in order to achievethe object described above have resulted in finding that theconstitution of a compound represented by Formula (1) shown below makesit possible to generate phosphorescent emission at a high efficiencybecause of a reason described later when it is used as a material for anorganic EL device and extend a lifetime of the device, and thus theyhave come to complete the present invention.

That is, the present invention relates to a material for an organicelectroluminescence device represented by Formula (1) shown below:

(in Formula (1), X¹ and X² each are independently an oxygen atom or asulfur atom, and they are not a sulfur atom at the same time; R¹ to R⁸each represent independently an alkyl group having 1 to 20 carbon atoms,a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy grouphaving 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 20 ringcarbon atoms, an aryl group having 6 to 18 ring carbon atoms, an aryloxygroup having 6 to 18 ring carbon atoms, a heteroaryl group having 5 to18 ring atoms, an amino group, a silyl group, a fluoro group or a cyanogroup, and the above substituents R¹ to R⁸ may be further substitutedwith the above substituents; when R¹ to R⁸ each are present in a pluralnumber, they may be the same as or different from each other;a, d, f and h each represent independently an integer of any of 0 to 4,and b, c, e and g each represent independently an integer of any of 0 to3; a sum of a to h is 6 or less;L¹ represents a single bond, a divalent linkage group containing N, adivalent linkage group containing O, a divalent linkage group containingSi, a divalent linkage group containing P, a divalent linkage groupcontaining S, an alkylene group having 1 to 20 carbon atoms, acycloalkylene group having 3 to 20 ring carbon atoms, an arylene grouphaving 6 to 18 ring carbon atoms, a heteroarylene group having 5 to 18ring atoms, a divalent amino group or a divalent silyl group;L² and L³ each represent independently a single bond, an alkylene grouphaving 1 to 20 carbon atoms, a cycloalkylene group having 3 to 20 ringcarbon atoms, an arylene group having 6 to 18 ring carbon atoms or aheteroarylene group having 5 to 18 ring atoms; L¹ to L³ may be furthersubstituted with any of the substituents R¹ to R⁸ described above;provided that when L¹ is an arylene group having 6 to 18 ring carbonatoms or a heteroarylene group having 5 to 18 ring atoms, a and d eachrepresent independently an integer of any of 1 to 4).

Further, the present invention relates to an organic electroluminescencedevice which is provided with one or more organic thin film layersincluding a light emitting layer between a cathode and an anode and inwhich at least one layer of the organic thin film layers described abovecontains the material for an organic electroluminescence devicerepresented by Formula (1) described above.

Effect of the Invention

According to the present invention, an organic EL device having a highefficiency in phosphorescent emission and a long lifetime and a materialfor an organic EL device which materializes the same can be provided.

EMBODIMENTS FOR CARRYING OUT THE INVENTION

The material for an organic electroluminescence device according to thepresent invention is represented by Formula (1) shown below:

(in Formula (1), X¹ and X² each are independently an oxygen atom or asulfur atom, and they are not a sulfur atom at the same time (that is,X¹ and X² are an oxygen atom or one of them is an oxygen atom, and theother is a sulfur atom); R¹ to R⁸ each represent independently an alkylgroup having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, acycloalkoxy group having 3 to 20 ring carbon atoms, an aryl group having6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbonatoms, a heteroaryl group having 5 to 18 ring atoms, an amino group, asilyl group, a fluoro group or a cyano group, and the above substituentsR¹ to R⁸ may be further substituted with the above substituents(hereinafter referred to as “the substituents R” as a whole); when R¹ toR⁸ each are present in a plural number, they may be the same as ordifferent from each other;a, d, f and h each represent independently an integer of any of 0 to 4,and b, c, e and g each represent independently an integer of any of 0 to3; a sum of a to h is 6 or less;L¹ represents a single bond, a divalent linkage group containing N, adivalent linkage group containing O, a divalent linkage group containingSi, a divalent linkage group containing P, a divalent linkage groupcontaining S, an alkylene group having 1 to 20 carbon atoms, acycloalkylene group having 3 to 20 ring carbon atoms, an arylene grouphaving 6 to 18 ring carbon atoms, a heteroarylene group having 5 to 18ring atoms, a divalent amino group or a divalent silyl group;L² and L³ each represent independently a single bond, an alkylene grouphaving 1 to 20 carbon atoms, a cycloalkylene group having 3 to 20 ringcarbon atoms, an arylene group having 6 to 18 ring carbon atoms or aheteroarylene group having 5 to 18 ring atoms; L¹ to L³ may be furthersubstituted with any of the substituents R described above; providedthat when L¹ is an arylene group having 6 to 18 ring carbon atoms or aheteroarylene group having 5 to 18 ring atoms, a and d each representindependently an integer of any of 1 to 4).

In particular, bonding of a dibenzofranyl group or a dibenzothiophenylgroup at an N-position (9-position) of a carbazolyl group directly orvia a bonding group as shown in Formula (1) elevates a LUMO sequence ofdibenzofrane or dibenzothiophene and makes it easy to inject electronsinto a light emitting layer and the like in the organic EL deviceprepared by using the material for an organic electroluminescence deviceaccording to the present invention. This makes it possible to facilitatecontrolling the carrier balance, and the effects of the presentinvention are exerted well.

The alkyl group represented by R¹ to R⁸ includes methyl, ethyl, propyl,isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl,n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl,n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl,neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl,1-heptyloctyl, 3-methylpentyl and the like.

The examples of the cycloalkyl group represented by R¹ to R⁸ includecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,norbornyl, adamantyl and the like.

The alkoxy group represented by R¹ to R⁸ includes methoxy, ethoxy,propoxy, butoxy, pentyloxy, hexyloxy and the like, and the groups having3 or more carbon atoms may be linear, cyclic or branched.

The cycloalkoxy group represented by R¹ to R⁸ includes cyclopentoxy,cyclohexyloxy and the like.

The aryl group represented by R¹ to R⁸ includes phenyl, tolyl, xylyl,mesityl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl,p-terphenyl, naphthyl, phenanthryl and the like. Among them, phenyl andmesityl are preferred.

The aryloxy group represented by R¹ to R⁸ includes, for example,phenoxy, biphenyloxy and the like.

The heteroaryl group represented by R¹ to R⁸ includes carbazolyl,dibenzofuranyl, dibenzothiophenyl, pyrrolyl, furyl, thienyl, silolyl,pyridyl, quinolyl, isoquinolyl, benzofuryl, imidazolyl, pyrimidyl,selenophenyl, oxadiazolyl, triazolyl and the like.

The amino group and the silyl group represented by R¹ to R⁸ may besubstituted with the substituents which have already been described. Thesilyl group is preferably trimethylsilyl.

It is preferred that a, d, f and h each are independently an integer ofany of 0 to 3, and they are more preferably an integer of any of 0 to 2.Also, it is preferred that b, c, e and g each are independently aninteger of any of 0 to 2, and they are more preferably an integer of anyof 0 to 1. Further, a sum of a to h is preferably 4 or less consideringthat if the sublimation property and the molecular weight are too large,thermal decomposition is liable to be brought about in vapor deposition.

The divalent linkage group containing N, the divalent linkage groupcontaining 0, the divalent linkage group containing Si, the divalentlinkage group containing P and the divalent linkage group containing Seach represented by L¹ include the following groups:

(in the respective formulas shown above, R^(x), R^(Y) and R^(z) each areindependently a hydrogen atom or a group selected from the substituentsR described above; and R^(x)′ is oxygen). Among the groups describedabove, a “—S—” group, a phosphoxide group and an ether group arepreferred.

The alkylene group, the cycloalkylene group having 3 to 20 ring carbonatoms, the arylene group having 6 to 18 ring carbon atoms, theheteroarylene group having 5 to 18 ring atoms, the divalent amino groupor the divalent silyl group each represented by L¹ to L³ include groupsobtained by substituting hydrogen atoms of one of the substituentsrepresented by R¹ to R⁸ with bonding sites. Also, in the presentinvention, 9,9-fluorenylidene is included as well in the arylene group.

The arylene group is suitably p-phenylene, m-phenylene and biphenylenein addition to groups described later, and the amino group is suitablybiphenylamino in addition to groups described later.

The linkage groups represented by L¹ to L³ may further havesubstituents, and the above substituents are equivalent to thesubstituents explained in the substituents represented by R¹ to R⁸.

The material for an organic EL device according to the present inventionis preferably a host material or a hole-transporting material which isused together with the phosphorescence luminescence material. Also, anenergy level of the triplet is preferably 2.0 eV or more, morepreferably 2.5 eV or more.

The material for an organic EL device according to the present inventionis preferably represented by the following Formula (2). A case in whichtwo carbazolyl groups are bonded at a 3-position directly or via alinkage group as is the case with the following Formula (2) has thefollowing advantages.

(1) The convenience in the synthesis is high.(2) The 3- and 6-positions of carbazole are sites which are inferior ina chemical stability, and introduction of a substituent other than ahydrogen atom into even one of the 3- and 6-positions makes it possibleto enhance the chemical stability. Accordingly, a structure in which asubstituent is further introduced into the 6-position is more preferred.(3) When carbazoles are combined at a 3-position via single bonds, Natoms on two carbazoles are conjugated to thereby make HOMO shallow, andthe hole-injecting and transporting property can be elevated to make iteasy to control the carrier balance.

(in Formula (2), X¹ and X², R¹ to R⁸, a to h and L¹ to L³ are the sameas described above).

Further, the material for an organic EL device according to the presentinvention is preferably represented by the following Formula (3) interms of further enhancing a chemical stability.

(in Formula (3), R^(1a), R^(4a), R^(6a), and R^(8a) each representindependently a hydrogen atom (corresponding to a case in which a, d, hand f in Formula (1) are 0) or an aryl group having 6 to 18 ring carbonatoms (the same aryl group as the substituent R described above), andthe above aryl group may be substituted with the substituents Rdescribed above; and X′, X² and L¹ to L³ are the same as describedabove).

Further, L² and L³ are preferably single bonds, and L¹ is preferably asingle bond as well. This is because if the sublimation property and themolecular weight are too large, thermal decomposition is liable to bebrought about in vapor deposition. Further, “L¹” and/or “L² and L³” arepreferably single bonds in terms of a reduction in the voltage and thehalf life. Also, X¹ and X² in Formulas (1) to (3) are preferably oxygenatoms in terms of the external quantum efficiency and the lifetime.

Further, Formula (3) is further preferably represented by the followingFormula (3a) in terms of a reduction in the voltage and the half life:

(in Formula (3a), R^(1a) and R^(4a) each represent independently ahydrogen atom or a phenyl group which may be substituted with methyl;L^(1a) is a single bond or a phenylene group; provided that a case inwhich both of R^(1a) and R^(4a) are hydrogen atoms and in which L^(1a)is a phenylene group is excluded).

In a case in which both of R^(1a) and R^(4a) are hydrogen atoms and inwhich L^(1a) is a phenylene group in Formula (3a) described above, ahydrogen atom is present at a 6-position of carbazole, and carbazolesare not bonded at a 3-position via a single bond. Accordingly, it is nota particularly excellent material as the material for an organicelectroluminescence device in terms of a chemical stability andcontrolling of a carrier balance.

The specific examples of the material for an organic EL devicerepresented by Formula (1) according to the present invention shall beshown below, but the present invention shall not be restricted to thesecompounds shown as the examples. Substituents shown in the followingspecific examples can be listed as the preferred substituents in thepresent invention.

Among the compounds shown above, the compounds (1), (2), (3), (4), (5),(7), (8), (13), (35), (36), (48), (49), (54), (55), (56), (59) and (60)are preferred, and the compounds (1), (2), (3), (8), (13), (54), (55),(56) and (60) are more preferred.

The material for an organic EL device according to the present inventionis preferably a host material contained in a light emitting layer of theorganic EL device.

Next, the organic EL device of the present invention shall be explained.

The organic EL device of the present invention has one or more organicthin film layers including a light emitting layer between a cathode andan anode, and at least one layer of the above organic thin film layerscontains the material for an organic EL device according to the presentinvention.

The structure of the organic EL device of a multilayer type includes,for example, structures in which layers are laminated in a multilayerconstitution, such as anode/hole transporting layer (hole injectinglayer)/light emitting layer/cathode, anode/light emitting layer/electrontransporting layer (electron injecting layer)/cathode, anode/holetransporting layer (hole injecting layer)/light emitting layer/electrontransporting layer (electron injecting layer)/cathode, anode/holetransporting layer (hole injecting layer)/light emitting layer/holeblocking layer/electron transporting layer (electron injectinglayer)/cathode and the like. In the present invention, “the holetransporting/hole injecting layer” is included in the mode of the holetransporting layer.

In the organic EL device of the present invention, the light emittinglayer described above contains preferably the material for an organic ELdevice represented by Formula (1) as a host material, and it containsmore preferably a phosphorescence luminescence material. Also, when theorganic EL device of the present invention has a hole transporting layer(hole injecting layer), the material for an organic EL device accordingto the present invention can preferably be contained as well in theabove hole transporting layer (hole injecting layer).

The phosphorescence luminescence material is preferably a compoundcontaining metal selected from iridium (Ir), osmium (Os) and platinum(Pt) in terms of having a high phosphorescence quantum efficiency andmaking it possible to enhance more an external quantum efficiency of thelight emitting device, and it is more preferably a metal complex such asan iridium complex, an osmium complex and a platinum complex. Amongthem, the iridium complex and the platinum complex are more preferred.The metal complexes described above are preferably ortho-metallizationmetal complexes in which a central metal atom is subjected toortho-metal bonding with a carbon atom contained in a ligand, andortho-metallation iridium complexes are more preferred. The furtherpreferred modes of the ortho-metallization metal complexes includeiridium complexes shown below.

Further, in the organic EL device of the present invention, the lightemitting layer described above contains preferably the host materialcontaining the material for an organic EL device according to thepresent invention and the phosphorescence luminescence material, and itcontains preferably a blue light emitting metal complex having a maximumvalue of 500 nm or less in an emission wavelength as the phosphorescenceluminescence material.

The organic EL device of the present invention has a hole transportinglayer (hole injecting layer), and the above hole transporting layer(hole injecting layer) preferably contains as well the material for anorganic EL device according to the present invention.

The organic EL device of the present invention contains preferably areducing dopant in an interfacial region between a cathode and anorganic thin film layer. The reducing dopant includes at least oneselected from alkali metals, alkali metal complexes, alkali metalcompounds, alkaline earth metals, alkaline earth metal complexes,alkaline earth metal compounds, rare earth metals, rare earth metalcomplexes, rare earth metal compounds and the like.

The alkali metal includes Na (work function: 2.36 eV), K (work function:2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV) andthe like, and the metals having a work function of 2.9 eV or less areparticularly preferred. Among them, K, Rb and Cs are preferred, and Rbor Cs is more preferred. Cs is most preferred.

The alkaline earth metals include Ca (work function: 2.9 eV), Sr (workfunction: 2.0 to 2.5 eV), Ba (work function: 2.52 eV) and the like, andthe metals having a work function of 2.9 eV or less are particularlypreferred.

The rare earth metals include Sc, Y, Ce, Tb, Yb and the like, and themetals having a work function of 2.9 eV or less are particularlypreferred.

Among the above metals, the preferred metals have a particularly highreducing ability, and addition thereof to an electron injecting zone ina relatively small amount makes it possible to enhance an emissionluminance and extend a lifetime in the organic EL device.

The alkali metal compounds include alkali oxides such as Li₂O, Cs₂O, K₂Oand the like, and alkali halides such as LiF, NaF, CsF, KF and the like.LiF, Li₂O and NaF are preferred.

The alkaline earth metal compounds include BaO, SrO, CaO andBa_(x)Sr_(1-x)O (0<x<1), Ba_(x)Ca_(1-x)O (0<x<1) and the like which areobtained by mixing the above compounds, and BaO, SrO and CaO arepreferred.

The rare earth metal compounds include YbF₃, ScF₃, Y₂O₃, Ce₂O₃, GdF₃,TbF₃ and the like, and YbF₃, ScF₃ and TbF₃ are preferred.

The alkali metal complexes, the alkaline earth metal complexes and therare earth metal complexes shall not specifically be restricted as longas they contain at least one metal ion of alkali metal ions, alkalineearth metal ions and rare earth metal ions. Preferred for the ligandsare quinolinol, benzoquinolinol, acridinol, phenanthridinol,hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole,hydroxydiarylthiadiazole, hydroxyphenylpyridine,hydroxyphenylbenzimidazole, hydroxybenzotriazole, hydroxyfurborane,bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene,β-diketones, azomethines and derivatives thereof, but they shall not berestricted to the above compounds.

In respect to an addition mode of the reducing dopant, it is formedpreferably in a layer shape or an island shape in an interfacial region.A forming method thereof is preferably a method in which whiledepositing the reducing dopant by a resistance heating depositionmethod, organic substances used as a light emitting material or anelectron injecting material for forming an interfacial region aredeposited at the same time to disperse the reducing dopant in theorganic substances. The dispersion concentration is the organicsubstances: the reducing dopant=100:1 to 1:100, preferably 5:1 to 1:5 interms of a molar ratio. When the reducing dopant is formed into a layershape, a light emitting material or an electron injecting material usedfor forming an organic layer in an interface are formed into a layershape, and then the reducing dopant is deposited separately by aresistance heating deposition method. The layer is formed preferably ina layer thickness of 0.1 to 15 nm. When the reducing dopant is formedinto an island shape, the light emitting material or the electroninjecting material used for forming an organic layer in an interface areformed into an island shape, and then the reducing dopant is depositedseparately by the resistance heating deposition method. The layer isformed preferably in an island thickness of 0.05 to 1 nm.

The organic EL device of the present invention has an electron injectinglayer between a light emitting layer and a cathode, and the aboveelectron injecting layer contains preferably a nitrogen-containingheterocyclic derivative as a principal component. An aromaticheterocyclic compound having at least one hetero atom in a molecule ispreferably used as an electron transporting material used for theelectron injecting layer, and a nitrogen-containing heterocyclicderivative is particularly preferred.

The above nitrogen-containing heterocyclic derivative is preferably, forexample, a nitrogen-containing heterocyclic metal chelate complexrepresented by Formula (A).

The above nitrogen-containing heterocyclic derivative is preferably, forexample, a nitrogen-containing heterocyclic metal chelate complexrepresented by Formula (A):

R¹⁰² to R¹⁰⁷ each are independently a hydrogen atom, a halogen atom, anamino group, a hydrocarbon group having 1 to 40 carbon atoms, an alkoxygroup, an aryloxy group, an alkoxycarbonyl group or a heterocyclicgroup, and they may be substituted.

The examples of the halogen atom include a fluorine atom, a chlorineatom, a bromine atom and an iodine atom. Also, The examples of the aminogroup which may be substituted include the same groups as in thealkylamino group and the arylamino group each described above. Further,it may be an aralkylamino group.

The hydrocarbon group having 1 to 40 carbon atoms include a substitutedor non-substituted alkyl group, an alkenyl group, a cycloalkyl group, anaryl group, an aralkyl group and the like. The examples of the alkylgroup, the cycloalkyl group, the alkoxy group, the aryl group, theheterocyclic group and the aryloxy group include the same groups asdescribed above. The alkenyl group includes groups corresponding to thealkyl groups described above. The aralkyl group include the alkyl groupsdescribed above which are substituted with the aryl groups describedabove. The alkoxycarbonyl group is represented by —COOY′, and theexamples of Y′ include the same groups as the alkyl groups describedabove.

M is aluminum (Al), gallium (Ga) or indium (In), and it is preferablyIn.

L in Formula (A) is a group represented by Formula (A′) or (A″) shownbelow:

(wherein R¹⁰⁸ to R¹¹² each are independently a hydrogen atom or asubstituted or non-substituted hydrocarbon group having 1 to 40 carbonatoms, and the groups which are adjacent to each other may form a cyclicstructure; further, R¹¹³ to R¹²⁷ each are independently a hydrogen atomor a substituted or non-substituted hydrocarbon group having 1 to 40carbon atoms, and the groups which are adjacent to each other may form acyclic structure).

The hydrocarbon group having 1 to 40 carbon atoms represented by R¹⁰⁸ toR¹¹² and R¹¹³ to R¹²⁷ in Formula (A′) and Formula (A″) includes the samegroups as the specific examples of R¹ to R⁸.

Also, a divalent group in a case where the groups adjacent to each otherin R¹⁰⁸ to R¹¹² and R¹¹³ to R¹²⁷ form a cyclic structure includestetramethylene, pentamethylene, hexamethylene,diphenylmethane-2,2′-diyl, diphenylethane-3,3′-diyl,diphenylpropane-4,4′-diyl and the like.

The specific examples of the nitrogen-containing heterocyclic metalchelate complex represented by Formula (A) shall be shown below, butthey shall not be restricted to these compounds shown as the examples.

The nitrogen-containing heterocyclic derivative includes as wellnitrogen-containing compounds which are nitrogen-containing heterocyclicderivatives comprising organic compounds having the following formulasand which are not metal complexes. It includes, for example,five-membered rings or six-membered rings having a skeleton representedby Formula (a) and derivatives having a structure represented by Formula(b):

(in Formula (b), X represents a carbon atom or a nitrogen atom; Z¹ andZ² each are independently an atomic group which can form anitrogen-containing heterocycle).

The nitrogen-containing heterocyclic derivative is preferably an organiccompound having a nitrogen-containing aromatic polycycle comprising afive-membered ring or a six-membered ring. Further, in a case of theabove nitrogen-containing aromatic polycycle having plural nitrogenatoms, it is a nitrogen-containing aromatic polycyclic organic compoundhaving a skeleton obtained by combining the structures represented byFormulas (a) and (b) described above.

The nitrogen-containing group of the nitrogen-containing organiccompound is selected from, for example, nitrogen-containing heterocyclicgroups represented by the following formulas:

(in the respective formulas, n groups of R²⁸ are present, and they arean aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms or analkoxy group having 1 to 20 carbon atoms; n showing the number of R²⁸ isan integer of 0 to 5, and when n is an integer of 2 or more, plural R²⁸may be the same as or different from each other).

Further, the preferred specific compounds include nitrogen-containingheterocyclic derivatives represented by the following Formula:

HAr^(a)-L⁶-Ar^(b)—Ar^(c)

(wherein HAr^(a) is a nitrogen-containing heterocycle having 3 to 40carbon atoms which may have a substituent; L⁶ is a single bond, anarylene group having 6 to 40 carbon atoms which may have a substituentor a heteroarylene group having 3 to 40 carbon atoms may have asubstituent; Ar^(b) is a divalent aromatic hydrocarbon group having 6 to40 carbon atoms which may have a substituent; and Ar^(c) is an arylgroup having 6 to 40 carbon atoms which may have a substituent or aheteroaryl group having 3 to 40 carbon atoms which may have asubstituent).

HAr^(a) is selected from, for example, the following group:

L⁶ is selected from, for example, the following group:

Ar^(c) is selected from, for example, the following group:

Ar^(b) is selected from, for example, the following aryl anthranylgroups:

(wherein R²⁹ to R⁴² each are independently a hydrogen atom, a halogenatom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having1 to 20 carbon atoms, an aryloxy group having 6 to 40 carbon atoms, anaryl group having 6 to 40 carbon atoms which may have a substituent or aheteroaryl group having 3 to 40 carbon atoms; and Ar^(d) is an arylgroup having 6 to 40 carbon atoms which may have a substituent or aheteroaryl group having 3 to 40 carbon atoms).

Also, preferred are the nitrogen-containing heterocyclic derivatives inwhich all of R²⁹ to R³⁶ in Ar^(b) represented by the formula shown aboveare hydrogen atoms.

In addition to the above compounds, the following compounds (refer toJapanese Patent Application Laid-Open No. 3448/1997) can suitably beused as well:

(wherein R⁴³ to R⁴⁶ each represent independently a hydrogen atom, asubstituted or non-substituted aliphatic group, a substituted ornon-substituted alicyclic group, a substituted or non-substitutedcarbocyclic aromatic group or a substituted or non-substitutedheterocyclic group; and X¹ and X² each represent independently an oxygenatom, a sulfur atom or a dicyanomethylene group).

Further, the following compounds (refer to Japanese Patent ApplicationLaid-Open No. 173774/2000) can suitably be used as well:

In the formula, R⁴⁷, R⁴⁸, R⁴⁹ and R⁵⁰ are groups which are the same asor different from each other, and they are an aryl group represented bythe following formula:

(wherein, R⁵¹, R⁵², R⁵³, R⁵⁴ and R⁵⁵ are groups which are the same as ordifferent from each other, and they are a hydrogen atom or one of themis a saturated or unsaturated alkoxyl group, an alkyl group, an aminogroup or an alkylamino group).

Further, the nitrogen-containing heterocyclic derivative may be apolymer compound containing the above nitrogen-containing heterocyclicgroup or nitrogen-containing heterocyclic derivative.

Also, the electron transporting layer contains preferably at least oneof nitrogen-containing heterocyclic derivatives represented by thefollowing Formulas (201) to (203):

In Formulas (201) to (203), R⁵⁶ is a hydrogen atom, an aryl group having6 to 60 carbon atoms which may have a substituent, a pyridyl group whichmay have a substituent, a quinolyl group which may have a substituent,an alkyl group having 1 to 20 carbon atoms which may have a substituentor an alkoxy group having 1 to 20 carbon atoms which may have asubstituent; n is an integer of 0 to 4; R⁵⁷ is an aryl group having 6 to60 carbon atoms which may have a substituent, a pyridyl group which mayhave a substituent, a quinolyl group which may have a substituent, analkyl group having 1 to 20 carbon atoms which may have a substituent oran alkoxy group having 1 to 20 carbon atoms; R⁵⁸ and R⁵⁹ each areindependently a hydrogen atom, an aryl group having 6 to 60 carbon atomswhich may have a substituent, a pyridyl group which may have asubstituent, a quinolyl group which may have a substituent, an alkylgroup having 1 to 20 carbon atoms which may have a substituent or analkoxy group having 1 to 20 carbon atoms which may have a substituent;L⁷ is a single bond, an arylene group having 6 to 60 carbon atoms whichmay have a substituent, a pyridinylene group which may have asubstituent, a quinolinylene group which may have a substituent or afluorenylene group which may have a substituent; Ar^(e) is an arylenegroup having 6 to 60 carbon atoms which may have a substituent, apyridinylene group which may have a substituent or a quinolinylene groupwhich may have a substituent; Ar^(f) is an aryl group having 6 to 60carbon atoms which may have a substituent, a pyridyl group which mayhave a substituent, a quinolyl group which may have a substituent, analkyl group having 1 to 20 carbon atoms which may have a substituent oran alkoxy group having 1 to 20 carbon atoms which may have asubstituent.

Ar^(g) is an aryl group having 6 to 60 carbon atoms which may have asubstituent, a pyridyl group which may have a substituent, a quinolylgroup which may have a substituent, an alkyl group having 1 to 20 carbonatoms which may have a substituent, an alkoxy group having 1 to 20carbon atoms which may have a substituent or a group represented by—Ar^(e)—Ar^(f) (Ar^(e) and Ar^(f) each are the same as described above).

In Formulas (201) to (203) described above, R⁵⁶ is a hydrogen atom, anaryl group having 6 to 60 carbon atoms which may have a substituent, apyridyl group which may have a substituent, a quinolyl group which mayhave a substituent, an alkyl group having 1 to 20 carbon atoms which mayhave a substituent or an alkoxy group having 1 to 20 carbon atoms whichmay have a substituent.

The aryl group having 6 to 60 carbon atoms described above is preferablyan aryl group having 6 to 40 carbon atoms, more preferably an aryl grouphaving 6 to 20 carbon atoms, and it includes, to be specific, monovalentgroups comprising phenyl, naphthyl, anthryl, phenanthryl, naphthacenyl,chrysenyl, pyrenyl, biphenyl, terphenyl, tolyl, t-butylphenyl,(2-phenylpropyl)phenyl, fluoranthenyl, fluorenyl and spirobifluorene,monovalent groups comprising perfluorophenyl, perfluoronaphthyl,perfluoroanthryl, perfluorobiphenyl and 9-phenylanthracene, monovalentgroups comprising 9-(1′-naphthyl)anthracene, monovalent groupscomprising 9-(2′-naphthyl)anthracene, monovalent groups comprising6-phenylchrysene, monovalent groups comprising9-[4-(diphenylamino)phenyl]anthracene and the like, and preferred arephenyl, naphthyl, biphenyl, terphenyl, 9-(10-phenyl)anthryl,9-[10-(1′-naphthyl)anthryl, 9-[10-(2′-naphthyl)anthryl and the like.

The alkyl group having 1 to 20 carbon atoms is preferably an alkyl grouphaving 1 to 6 carbon atoms, and it includes, to be specific, methyl,ethyl, propyl, butyl, pentyl, hexyl and the like, and in additionthereto, it includes haloalkyl groups such as trifluoromethyl and thelike. The alkyl groups having 3 or more carbon atoms may be linear,cyclic or branched.

The alkoxy group having 1 to 20 carbon atoms is preferably an alkoxygroup having 1 to 6 carbon atoms, and it includes, to be specific,methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy and the like, andthe alkoxy groups having 3 or more carbon atoms may be linear, cyclic orbranched.

The substituents of the respective groups represented by R⁵⁶ include ahalogen atom, an alkyl group having 1 to 20 carbon atoms which may havea substituent, an alkoxy group having 1 to 20 carbon atoms which mayhave a substituent, an aryloxy group having 6 to 40 carbon atoms whichmay have a substituent, an aryl group having 6 to 40 carbon atoms whichmay have a substituent or a heteroaryl group having 3 to 40 carbon atomswhich may have a substituent The halogen atom includes fluorine,chlorine, bromine and iodine.

The alkyl group having 1 to 20 carbon atoms, the alkoxy group having 1to 20 carbon atoms and the aryl group having 6 to 40 carbon atomsinclude the same groups as described above.

The aryloxy group having 6 to 40 carbon atoms includes, for example,phenoxy, biphenyloxy and the like.

The heteroaryl group having 6 to 40 carbon atoms includes, for example,pyrrolyl, furyl, thienyl, silolyl, pyridyl, quinolyl, isoquinolyl,benzofuryl, imidazolyl, pyrimidyl, carbazolyl, selenophenyl,oxadiazolyl, triazolyl and the like.

The term n is an integer of 0 to 4, preferably 0 to 2.

In Formula (201) described above, R⁵⁷ is an aryl group having 6 to 60carbon atoms which may have a substituent, a pyridyl group which mayhave a substituent, a quinolyl group which may have a substituent, analkyl group having 1 to 20 carbon atoms which may have a substituent oran alkoxy group having 1 to 20 carbon atoms which may have asubstituent.

The specific examples, the preferred carbon numbers and the substituentsof the above respective groups are the same as those explained for Rdescribed above.

In Formulas (202) and (203) described above, R⁵⁸ and R⁵⁹ each areindependently a hydrogen atom, an aryl group having 6 to 60 carbon atomswhich may have a substituent, a pyridyl group which may have asubstituent, a quinolyl group which may have a substituent, an alkylgroup having 1 to 20 carbon atoms which may have a substituent or analkoxy group having 1 to 20 carbon atoms which may have a substituent.

The specific examples, the preferred carbon numbers and the substituentsof the above respective groups are the same groups as those explainedfor R⁵⁶ described above.

In Formulas (201) to (203) described above, L⁷ is a single bond, anarylene group having 6 to 60 carbon atoms which may have a substituent,a pyridinylene group which may have a substituent, a quinolinylene groupwhich may have a substituent or a fluorenylene group which may have asubstituent.

The arylene group having 6 to 60 carbon atoms is preferably an arylenegroup having 6 to 40 carbon atoms, more preferably an arylene grouphaving 6 to 20 carbon atoms, and it includes, to be specific, divalentgroups formed by removing one hydrogen atom from the aryl groupsexplained for R described above.

The substituents of the respective groups represented by L⁷ are the samegroups as those explained for R⁵⁶ described above.

Further, L⁷ is preferably a group selected from the group consisting of:

In Formula (201) described above, Ar^(e) is an arylene group having 6 to60 carbon atoms which may have a substituent, a pyridinylene group whichmay have a substituent or a quinolinylene group which may have asubstituent. The substituents of the respective groups represented byAr^(e) and Ar^(g) each are the same as those explained for R describedabove.

Also, Ar^(e) is preferably any group selected from condensed ring groupsrepresented by the following Formulas (101) to (110):

In Formulas (101) to (110) described above, the respective condensedrings may be combined with a bonding group comprising a halogen atom, analkyl group having 1 to 20 carbon atoms which may have a substituent, analkoxy group having 1 to 20 carbon atoms which may have a substituent,an aryloxy group having 6 to 40 carbon atoms which may have asubstituent, an aryl group having 6 to 40 carbon atoms which may have asubstituent or a heteroaryl group having 3 to 40 carbon atoms which mayhave a substituent, and when a plurality of the above bonding groups ispresent, the above bonding groups may be the same as or different fromeach other. The specific examples of the above respective groups includethe same groups as described above.

In Formula (101) described above, L′ is a single bond or a groupselected from the group consisting of:

Ar^(e) represented by Formulas (103) described above is preferablycondensed ring groups represented by the following Formulas (111) to(125):

In Formulas (111) to (125) described above, the respective condensedrings may be combined with a bonding group comprising a halogen atom, analkyl group having 1 to 20 carbon atoms which may have a substituent, analkoxy group having 1 to 20 carbon atoms which may have a substituent,an aryloxy group having 6 to 40 carbon atoms which may have asubstituent, an aryl group having 6 to 40 carbon atoms which may have asubstituent or a heteroaryl group having 3 to 40 carbon atoms which mayhave a substituent, and when a plurality of the above bonding groups ispresent, the above bonding groups may be the same as or different fromeach other. The specific examples of the above respective groups includethe same groups as described above.

In Formula (201) described above, Ar^(f) is an aryl group having 6 to 60carbon atoms which may have a substituent, a pyridyl group which mayhave a substituent, a quinolyl group which may have a substituent, analkyl group having 1 to 20 carbon atoms which may have a substituent oran alkoxy group having 1 to 20 carbon atoms which may have asubstituent.

The specific examples, the preferred carbon numbers and the substituentsof the above respective groups are the same as those explained for R⁵⁶described above.

In Formulas (202) and (203) described above, Ar^(g) is an aryl grouphaving 6 to 60 carbon atoms which may have a substituent, a pyridylgroup which may have a substituent, a quinolyl group which may have asubstituent, an alkyl group having 1 to 20 carbon atoms which may have asubstituent, an alkoxy group having 1 to 20 carbon atoms which may havea substituent or a group represented by —Ar^(e)—Ar^(f) (Ar^(e) andAr^(f) each are the same as described above).

The specific examples, the preferred carbon numbers and the substituentsof the above respective groups are the same as those explained for R⁵⁶described above.

Also, Ar^(g) is preferably any group selected from condensed ring groupsrepresented by the following Formulas (126) to (135):

In Formulas (126) to (135) described above, the respective condensedrings may be combined with a bonding group comprising a halogen atom, analkyl group having 1 to 20 carbon atoms which may have a substituent, analkoxy group having 1 to 20 carbon atoms which may have a substituent,an aryloxy group having 6 to 40 carbon atoms which may have asubstituent, an aryl group having 6 to 40 carbon atoms which may have asubstituent or a heteroaryl group having 3 to 40 carbon atoms which mayhave a substituent, and when a plurality of the above bonding groups ispresent, the above bonding groups may be the same as or different fromeach other. The specific examples of the above respective groups includethe same groups as described above.

In Formula (135) described above, L′ is the same as described above.

In Formulas (126) to (135) described above, R′ is a hydrogen atom, analkyl group having 1 to 20 carbon atoms which may have a substituent, anaryl group having 6 to 40 carbon atoms which may have a substituent or aheteroaryl group having 3 to 40 carbon atoms which may have asubstituent. The specific examples of the above respective groupsinclude the same groups as described above.

Ar^(g) represented by Formula (128) is preferably condensed ring groupsrepresented by the following Formulas (136) to (158):

In Formulas (126) to (135) described above, the respective condensedrings may be combined with a bonding group comprising a halogen atom, analkyl group having 1 to 20 carbon atoms which may have a substituent, analkoxy group having 1 to 20 carbon atoms which may have a substituent,an aryloxy group having 6 to 40 carbon atoms which may have asubstituent, an aryl group having 6 to 40 carbon atoms which may have asubstituent or a heteroaryl group having 3 to 40 carbon atoms which mayhave a substituent, and when a plurality of the above bonding groups ispresent, the above bonding groups may be the same as or different fromeach other. The specific examples of the above respective groups includethe same groups as described above. R′ is the same as described above.

Further, it is preferred that Ar^(f) and Ar^(g) each are independently agroup selected from the group consisting of:

The specific examples of the nitrogen-containing heterocyclic derivativeof the present invention represented by Formulas (201) to (203)described above shall be shown below, but the present invention shallnot be restricted to these compounds shown as the examples.

In the following tables, HAr represents:

in Formulas (201) to (203) described above.

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 1-1

2

3

4

5

6

7

8

9

10

11

12

13

14

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 2-1

2

3

4

5

6

7

8

9

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 3-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 4-1

2

3

4

5

6

7

8

9

10

11

12

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 5-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 6-1

2

3

4

5

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 7-1

2

3

4

5

6

7

8

9

10

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 8-1

2

3

4

5

6

7

8

9

10

11

12

13

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 9-1

2

3

4

5

6

7

8

9

10

11

12

13

14

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 10-1

2

3

4

5

6

7

8

9

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 11-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 12-1

2

3

4

5

6

7

8

9

10

11

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 13-1

2

3

4

5

6

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 14-1

2

3

4

5

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 15-1

2

3

4

5

6

7

8

9

10

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 16-1

2

3

4

5

6

7

8

HAr—L⁷—Ar^(e)—Ar^(f) HAr L⁷ Ar^(e) Ar^(f) 17-1

2

3

4

5

6

7

8

Among the above specific examples, (1-1), (1-5), (1-7), (2-1), (3-1),(4-2), (4-6), (7-2), (7-7), (7-8), (7-9), (9-1) and (9-7) areparticularly preferred.

Further, the nitrogen-containing heterocyclic derivative preferablyincludes as well nitrogen-containing five-membered ring derivatives. Theabove five-membered ring includes, for example, an imidazole ring, atriazole ring, a tetrazole ring, an oxazole ring, a thiadiazole ring, anoxatriazole ring, a thiatriazole ring and the like, and thenitrogen-containing five-membered ring derivative includes abenzimidazole ring, a benzotriazole ring, a pyridinoimidazole ring, apyrimidinoimidazole ring and a pyridazinoimidazole ring. Derivativesrepresented by the following Formula (B) are particularly preferred.

In Formula (B), L^(B) represents a divalent or more linkage group andincludes, for example, a carbon atom, a silicon atom, a nitrogen atom, aboron atom, an oxygen atom, a sulfur atom, a metal atom (for example, abarium atom, a beryllium atom), an aromatic hydrocarbon ring, anaromatic heterocycle and the like. Among them, a carbon atom, a nitrogenatom, a silicon atom, a boron atom, an oxygen atom, a sulfur atom, anaromatic hydrocarbon ring and an aromatic heterocycle are preferred, anda carbon atom, a silicon atom, an aromatic hydrocarbon ring and anaromatic heterocycle are more preferred.

The aromatic hydrocarbon rings and the aromatic heterocycles representedby L^(B) may have substituents, and the above substituents arepreferably an alkyl group, an alkenyl group, an alkynyl group, an arylgroup, an amino group, an alkoxy group, an aryloxy group, an acyl group,an alkoxycarbonyl group, an aryloxycarbonyl group, an acylxoy group, anacylamino group, an alkoxycarbonylamino group, an aryloxycarbonylaminogroup, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, analkylthio group, an arylthio group, a sulfonyl group, a halogen atom, acyano group and an aromatic heterocycle, more preferably an alkyl group,an aryl group, an alkoxy group, an aryloxy group, a halogen atom, acyano group and an aromatic heterocycle, further preferably an alkylgroup, an aryl group, an alkoxy group, an aryloxy group and an aromaticheterocycle and particularly preferably an alkyl group, an aryl group,an alkoxy group and an aromatic heterocycle.

The specific examples of L^(B) include groups shown below:

X^(B2) in Formula (B) represents —O—, —S— or —N(R^(B2))—. R^(B2)represents a hydrogen atom, an aliphatic hydrocarbon group, an arylgroup or a heterocyclic group.

The aliphatic hydrocarbon group represented by R^(B2) is a linear orbranched alkyl group (it is an alkyl group having preferably 1 to 20carbon atoms, more preferably 1 to 12 carbon atoms and particularlypreferably 1 to 8 carbon atoms and includes, for example, methyl, ethyl,isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl and the like), acycloalkyl group (it has preferably 3 to 10 ring carbon atoms andincludes, for example, cyclopropyl, cyclopentyl, cyclohexyl and thelike), an alkenyl group (it is an alkenyl group having preferably 2 to20 carbon atoms, more preferably 2 to 12 carbon atoms and particularlypreferably 2 to 8 carbon atoms and includes, for example, vinyl, allyl,2-butenyl, 3-pentenyl and the like) and an alkynyl group (it is analkynyl group having preferably 2 to 20 carbon atoms, more preferably 2to 12 carbon atoms and particularly preferably 2 to 8 carbon atoms andincludes, for example, propargyl, 3-pentynyl and the like), and alkylgroups are preferred.

The aryl group represented by R^(B2) is a single ring or a condensedring, and it is preferably an aryl group having preferably 6 to 30 ringcarbon atoms, more preferably 6 to 20 ring carbon atoms and furtherpreferably 6 to 12 ring carbon atoms. It includes, for example, phenyl,2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl,3-trifluoromethylphenyl, pentafluorophenyl, 1-naphthyl, 2-naphthyl andthe like, and phenyl and 2-methylphenyl are preferred.

The heterocyclic group represented by R^(B2) is a single ring or acondensed ring, and it is preferably a heterocyclic group havingpreferably 1 to 20 ring carbon atoms, more preferably 1 to 12 ringcarbon atoms and further preferably 2 to 10 ring carbon atoms and is anaromatic heterocyclic group containing at least one hetero atom of anitrogen atom, an oxygen atom, a sulfur atom and a selenium atom. Theexamples of the above heterocyclic group include, for example, groupsderived from pyrrolidine, piperidine, piperazine, morpholine, thiophene,selenophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine,pyridazine, pyrimidine, triazole, triazine, indole, indazole, purine,thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole,quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline,quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine,tetrazole, benzomidazole, benzoxazole, benzothiazole, benzotriazole,tetrazaindene, carbazole, azepine and the like, and they are preferablygroups derived from furan, thiophene, pyridine, pyrazine, pyrimidine,pyridazine, triazine, quinoline, phthalazine, naphthyridine, quinoxalineand quinazoline, more preferably groups derived from furan, thiophene,pyridine and quinoline. It is further preferably quinolinyl.

The aliphatic hydrocarbon group, the aryl group and the heterocyclicgroup each represented by R^(B2) may have substituents, and the abovesubstituents are preferably an alkyl group, an alkenyl group, an alkynylgroup, an aryl group, an amino group, an alkoxy group, an aryloxy group,an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, anacylxoy group, an acylamino group, an alkoxycarbonylamino group, anaryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, acarbamoyl group, an alkylthio group, an arylthio group, a sulfonylgroup, a halogen atom, a cyano group and an aromatic heterocycle, morepreferably an alkyl group, an aryl group, an alkoxy group, an aryloxygroup, a halogen atom, a cyano group and an aromatic heterocycle,further preferably an alkyl group, an aryl group, an alkoxy group, anaryloxy group and an aromatic heterocycle and particularly preferably analkyl group, an aryl group, an alkoxy group and an aromatic heterocycle.

R^(B2) is preferably an aliphatic hydrocarbon group, an aryl group or aheterocyclic group, more preferably an aliphatic hydrocarbon group (thegroup having preferably 6 to 30 carbon atoms, more preferably 6 to 20carbon atoms and further preferably 6 to 12 carbon atoms) or an arylgroup and further preferably an aliphatic hydrocarbon group (the grouphaving preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbonatoms and further preferably 2 to 10 carbon atoms). X^(B2) is preferably—O— or —N(R^(B2))—, more preferably —N(R^(B2))—.

Z^(B2) represents an atomic group necessary for forming an aromaticring. The aromatic ring formed by Z^(B2) may be any of an aromatichydrocarbon ring and an aromatic heterocycle, and the specific examplesthereof include, for example, a benzene ring, a pyridine, a pyrazinering, a pyrimidine ring, a pyridazine ring, a triazine ring, a pyrrolering, a furan ring, a thiophene ring, a selenophene ring, a tellurophenering, an imidazole ring, a thiazole ring, a selenazole ring, a tetrazolering, a thiadiazole ring, an oxadiazole ring, a pyrazole ring and thelike, and they are preferably a benzene ring, a pyridine, a pyrazinering, a pyrimidine ring and a pyridazine ring, more preferably a benzenering, a pyridine ring and a pyrazine ring, further preferably a benzenering and a pyridine ring and particularly preferably a pyridine ring.

The aromatic ring formed by Z^(B2) may further form condensed rings withother rings and may have a substituent. The substituents are the same asthe groups listed as the substituents of the groups represented by L^(B)described above, and they are preferably an alkyl group, an alkenylgroup, an alkynyl group, an aryl group, an amino group, an alkoxy group,an aryloxy group, an acyl group, an alkoxycarbonyl group, anaryloxycarbonyl group, an acylxoy group, an acylamino group, analkoxycarbonylamino group, an aryloxycarbonylamino group, asulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthiogroup, an arylthio group, a sulfonyl group, a halogen atom, a cyanogroup and an aromatic heterocycle, more preferably an alkyl group, anaryl group, an alkoxy group, an aryloxy group, a halogen atom, a cyanogroup and an aromatic heterocycle, further preferably an alkyl group, anaryl group, an alkoxy group, an aryloxy group and an aromaticheterocycle and particularly preferably an alkyl group, an aryl group,an alkoxy group and an aromatic heterocycle.

The term n^(B2) is an integer of 1 to 4, preferably 2 to 3.

Among the nitrogen-containing five-membered ring derivatives representedby Formula (B) described above, derivatives represented by Formula (B′)shown below are more preferred:

In Formula (B′), R^(B71), R^(B72) and R^(B73) each are the same asR^(B2) in Formula (B), and the preferred ranges are the same as well.

Z^(B71), Z^(B72), and Z^(B73) each are the same as Z^(B2) in Formula(B), and the preferred ranges are the same as well.

L^(B71), L^(B72), and L^(B73) each represent a linkage group and includegroups obtained by turning the examples of L^(B) in Formula (B) intodivalent groups, and they are preferably linkage groups comprising asingle bond, a divalent aromatic hydrocarbon ring group, a divalentaromatic heterocyclic group and combinations thereof, more preferablysingle bonds. L^(B71), L^(B72) and L^(B73) may have substituents. Theabove substituents are the same as the groups listed as the substituentsof the groups represented by L^(B) in Formula (B) described above, andthe preferred substituents are the same as well.

Y^(B) represents a nitrogen atom, a 1,3,5-benzenetoluoyl group or a2,4,6-triazinetoluoyl group. The 1,3,5-benzenetoluoyl group may havesubstituents at 2, 4 and 6-positions, and the substituents include, forexample, an alkyl group, an aromatic hydrocarbon ring group, a halogenatom and the like.

The specific examples of the nitrogen-containing five-membered ringderivative represented by Formula (B) or Formula (B′) shall be shownbelow, but they shall not be restricted to these compounds shown as theexamples:

The compounds constituting the electron injecting layer and the electrontransporting layer include as well compounds having a structure in whichan electron deficient nitrogen-containing five-membered ring or anelectron deficient nitrogen-containing six-membered ring skeleton iscombined with a substituted or non-substituted indole skeleton, asubstituted or non-substituted carbazole skeleton and a substituted ornon-substituted azacarbazole skeleton. Also, the suitable electrondeficient nitrogen-containing five-membered ring or electron deficientnitrogen-containing six-membered ring skeleton includes, for example,pyridine, pyrimidine, pyrazine, triazine, triazole, oxadiazole,pyrazole, imidazole, quinoxaline and pyrrole skeletons and molecularskeletons such as benzimidazole, imidazopyridine and the like eachobtained by combining the above skeletons with each other. Among theabove combinations, they include preferably combinations of pyridine,pyrimidine, pyrazine and triazine skeletons with carbazole, indole,azacarbazole and quinoxaline skeletons. The skeletons described abovemay be either substituted or non-substituted.

The specific examples of the electron transporting compound shall beshown below but shall not be restricted to these compounds:

The electron injecting layer and the electron transporting layer mayhave either a single layer structure comprising at least one of thematerials described above or a multilayer structure comprising plurallayers having the same composition or different compositions. Thematerials of the above layers have preferably a it electron deficientnitrogen-containing heterocyclic group.

Further, an insulator or a semiconductor in addition to thenitrogen-containing ring derivative is preferably used as a constituentfor the electron injecting layer. If the electron injecting layer isconstituted from an insulator and a semiconductor, an electric currentcan effectively be prevented from leaking to enhance the electroninjecting property.

Preferably used as the above insulator is at least one metal compoundselected from the group consisting of alkali metal chalcogenides,alkaline earth metal chalcogenides, halides of alkali metals and halidesof alkaline earth metals. If the electron injecting layer is constitutedfrom the above alkali metal chalcogenides and the like, it is preferredin terms of making it possible to enhance further the electron injectingproperty. To be specific, the preferred alkali metal chalcogenidesinclude, for example, Li₂O, K₂O, Na₂S, Na₂Se and Na₂O, and the preferredalkaline earth metal chalcogenides include, for example, CaO, BaO, SrO,BeO, BaS and CaSe. Further, the preferred halides of alkali metalsinclude, for example, LiF, NaF, KF, LiCl, KCl, NaCl and the like. Also,the preferred halides of alkaline earth metals include, for example,fluorides such as CaF₂, BaF₂, SrF₂, Mg₂, BeF₂ and the like and halidesother than the fluorides.

The semiconductor includes, for example, oxides, nitrides andoxynitrides each containing at least one element selected from the groupconsisting of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb andZn, and they may be used alone or in combination of two or more kindsthereof. Also, the inorganic compound constituting the electroninjecting layer is preferably a fine crystalline or amorphous insulatingthin film. If the electron injecting layer is constituted from the aboveinsulating thin film, the more homogeneous thin film is formed, andtherefore pixel defects such as dark spots and the like can be reduced.The above inorganic compound includes, for example, alkali metalchalcogenides, alkaline earth metal chalcogenides, halides of alkalimetals and halides of alkaline earth metals.

Further, the reducing dopant described above can preferably be added tothe electron injecting layer in the present invention.

A film thickness of the electron injecting layer or the electrontransporting layer shall not specifically be restricted, and it ispreferably 1 to 100 nm.

An aromatic amine compound, for example, an aromatic amine derivativerepresented by Formula (I) is suitably used in the hole injecting layeror the hole transporting layer (including the hole injectingtransporting layer):

In Formula (I), Ar¹ to Ar⁴ represent a substituted or non-substitutedaryl group having 6 to 50 ring carbon atoms or a substituted ornon-substituted heterocyclic group having 5 to 50 ring atoms.

The substituted or non-substituted aryl group having 6 to 50 ring carbonatoms includes, for example, phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl,2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl,4-phenanthryl, 9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl,9-naphthacenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenylyl,3-biphenylyl, 4-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl,p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl,o-tolyl, m-tolyl, p-tolyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl,3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthryl,4′-methylbiphenylyl, 4″-t-butyl-p-terphenyl-4-yl, fluoranthenyl,fluorenyl and the like.

The substituted or non-substituted heterocyclic group having 5 to 50ring atoms includes, for example, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl,pyrazinyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl,3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl,2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl,7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl,4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl,1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl,5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, quinolyl,3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl,1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl,6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl,5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl,3-carbazolyl, 4-carbazolyl, 9-carbazolyl, 1-phenanthridinyl,2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl,6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl,9-phenanthridinyl, 10-phenanthryldinyl, 1-acridinyl, 2-acridinyl,3-acridinyl, 4-acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl,1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl,1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl,1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl,1,7-phenanthroline-10-yl, 1,8-phenanthroline-2-yl,1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl,1,8-phenanthroline-5-yl, 1,8-phenanthroline-6-yl,1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl,1,8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl,1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl,1,9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl,1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl,1,9-phenanthroline-10-yl, 1,10-phenanthroline-2-yl,1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl,1,10-phenanthroline-5-yl, 2,9-phenanthroline-1-yl,2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl,2,9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl,2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl,2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl,2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl,2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl,2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl,2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl,2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl,2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl,2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl,2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazinyl,2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 10-phenothiazinyl,1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl,10-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl,5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl,2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl,3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl,3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl,3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl,2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl,4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl and thelike. It includes preferably phenyl, naphthyl, biphenyl, anthranyl,phenanthryl, pyrenyl, chrysenyl, fluoranthenyl, fluorenyl and the like.

L is a linkage group. To be specific, it is a substituted ornon-substituted arylene group having 6 to 50 ring carbon atoms, asubstituted or non-substituted heteroarylene group having 5 to 50 ringatoms or a divalent group obtained by combining two or more arylenegroups or heteroarylene groups with a single bond, an ether bond, athioether bond, an alkylene group having 1 to 20 carbon atoms, analkenylene group having 2 to 20 carbon atoms and an amino group. Thearylene group having 6 to 50 ring carbon atoms includes, for example,1,4-phenylene, 1,2-phenylene, 1,3-phenylene, 1,4-naphthylene,2,6-naphthylene, 1,5-naphthylene, 9,10-anthranylene,9,10-phenanthrenylene, 3,6-phenanthrenylene, 1,6-pyrenylene,2,7-pyrenylene, 6,12-chrysenylene, 4,4′-biphenylene, 3,3′-biphenylene,2,2′-biphenylene, 2,7-fluorenylene and the like. The heteroarylene grouphaving 5 to 50 ring atoms includes, for example, 2,5-thiophenylene,2,5-siloylene, 2,5-oxadiazolylene and the like. Preferred are1,4-phenylene, 1,2-phenylene, 1,3-phenylene, 1,4-naphthylene,9,10-anthranylene, 6,12-chrysenylene, 4,4′-biphenylene,3,3′-biphenylene, 2,2′-biphenylene and 2,7-fluorenylene.

When L is a linkage group comprising two or more arylene groups orheteroarylene groups, the adjacent arylene groups or heteroarylenegroups may be combined with each other via a divalent group to form anew ring. The examples of the divalent group for forming the ringincludes tetramethylene, pentamethylene, hexamethylene,diphenylmethane-2,2′-diyl, diphenylmethane-3,3′-diyl,diphenylpropane-4,4′-diyl and the like.

The substituents of Ar¹ to Ar⁴ and L are a substituted ornon-substituted aryl group having 6 to 50 ring carbon atoms, asubstituted or non-substituted heterocyclic group having 5 to 50 ringatoms, a substituted or non-substituted alkyl group having 1 to 50carbon atoms, a substituted or non-substituted cycloalkyl group having 3to 50 carbon atoms, a substituted or non-substituted alkoxy group having1 to 50 carbon atoms, a substituted or non-substituted aralkyl grouphaving 7 to 50 carbon atoms, a substituted or non-substituted aryloxygroup having 6 to 50 ring carbon atoms, a substituted or non-substitutedheteroaryloxy group having 5 to 50 ring atoms, a substituted ornon-substituted arylthio group having 6 to 50 ring carbon atoms, asubstituted or non-substituted heteroarylthio group having 5 to 50 ringatoms, a substituted or non-substituted alkoxycarbonyl group having 2 to50 carbon atoms, an amino group substituted with a substituted ornon-substituted aryl group having 6 to 50 ring carbon atoms or asubstituted or non-substituted heterocyclic group having 5 to 50 ringatoms, a halogen group, a cyano group, a nitro group, a hydroxyl groupand the like.

The examples of the substituted or non-substituted aryl group having 6to 50 ring carbon atoms include phenyl, 1-naphthyl, 2-naphthyl,1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl,3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacenyl,2-naphthacenyl, 9-naphthacenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl,2-biphenylyl, 3-biphenylyl, 4-biphenylyl, p-terphenyl-4-yl,p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl,m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-t-butylphenyl,p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl,4-methyl-1-anthryl, 4′-methylbiphenylyl, 4″-t-butyl-p-terphenyl-4-yl,fluoranthenyl, fluorenyl and the like.

The examples of the substituted or non-substituted heterocyclic grouphaving 5 to 50 ring atoms include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl,pyrazinyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl,3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl,2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl,7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl,4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl,1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl,5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, quinolyl,3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl,1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl,6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl,5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl,3-carbazolyl, 4-carbazolyl, 9-carbazolyl, 1-phenanthridinyl,2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl,6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl,9-phenanthridinyl, 10-phenanthryldinyl, 1-acridinyl, 2-acridinyl,3-acridinyl, 4-acridinyl, 9-acridinyl, 1,7-phenanthroline-2-yl,1,7-phenanthroline-3-yl, 1,7-phenanthroline-4-yl,1,7-phenanthroline-5-yl, 1,7-phenanthroline-6-yl,1,7-phenanthroline-8-yl, 1,7-phenanthroline-9-yl,1,7-phenanthroline-10-yl, 1,8-phenanthroline-2-yl,1,8-phenanthroline-3-yl, 1,8-phenanthroline-4-yl,1,8-phenanthroline-5-yl, 1,8-phenanthroline-6-yl,1,8-phenanthroline-7-yl, 1,8-phenanthroline-9-yl,1,8-phenanthroline-10-yl, 1,9-phenanthroline-2-yl,1,9-phenanthroline-3-yl, 1,9-phenanthroline-4-yl,1,9-phenanthroline-5-yl, 1,9-phenanthroline-6-yl,1,9-phenanthroline-7-yl, 1,9-phenanthroline-8-yl,1,9-phenanthroline-10-yl, 1,10-phenanthroline-2-yl,1,10-phenanthroline-3-yl, 1,10-phenanthroline-4-yl,1,10-phenanthroline-5-yl, 2,9-phenanthroline-1-yl,2,9-phenanthroline-3-yl, 2,9-phenanthroline-4-yl,2,9-phenanthroline-5-yl, 2,9-phenanthroline-6-yl,2,9-phenanthroline-7-yl, 2,9-phenanthroline-8-yl,2,9-phenanthroline-10-yl, 2,8-phenanthroline-1-yl,2,8-phenanthroline-3-yl, 2,8-phenanthroline-4-yl,2,8-phenanthroline-5-yl, 2,8-phenanthroline-6-yl,2,8-phenanthroline-7-yl, 2,8-phenanthroline-9-yl,2,8-phenanthroline-10-yl, 2,7-phenanthroline-1-yl,2,7-phenanthroline-3-yl, 2,7-phenanthroline-4-yl,2,7-phenanthroline-5-yl, 2,7-phenanthroline-6-yl,2,7-phenanthroline-8-yl, 2,7-phenanthroline-9-yl,2,7-phenanthroline-10-yl, 1-phenazinyl, 2-phenazinyl, 1-phenothiazinyl,2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, 10-phenothiazinyl,1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl,10-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl,5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl,2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl,3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl,3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl,3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl,2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl,4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl and thelike.

The examples of the substituted or non-substituted alkyl group having 1to 50 carbon atoms include methyl, ethyl, propyl, isopropyl, n-butyl,s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl,hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl,1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl,1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl,2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl,2,3-dichloro-t-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl,2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl,2,3-dibromo-t-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl,2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl,2,3-diiodo-t-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl,2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl,2,3-diamino-t-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl,2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl,2,3-dicyano-t-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl,2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl,2,3-dinitro-t-butyl, 1,2,3-trinitropropyl and the like.

The examples of the substituted or non-substituted cycloalkyl grouphaving 3 to 50 carbon atoms include cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 1-adamantyl, 2-adamantyl,1-norbornyl, 2-norbornyl and the like.

The substituted or non-substituted alkoxy group having 1 to 50 carbonatoms is a group represented by —OY. The examples of Y include methyl,ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl,n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl,2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl,1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl,chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl,1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl,1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl,2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl,2,3-dibromo-t-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl,2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl,2,3-diiodo-t-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl,2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl,2,3-diamino-t-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl,2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl,2,3-dicyano-t-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl,2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl,2,3-dinitro-t-butyl, 1,2,3-trinitropropyl and the like.

The examples of the substituted or non-substituted aralkyl group having7 to 50 carbon atoms include benzyl, 1-phenylethyl, 2-phenylethyl,1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl,1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl,2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl,2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl,1-pyrrolylmethyl, 2-(1-pyrrolyl)ethyl, p-methylbenzyl, m-methylbenzyl,o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl,p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl,o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl,p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl,m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl,o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, 1-chloro-2-phenylisopropyland the like.

The substituted or non-substituted aryloxy group having 6 to 50 ringcarbon atoms is represented by —OY′, and the examples of Y′ includephenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl,1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl,9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl,1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenylyl, 3-biphenylyl,4-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl,m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl,p-tolyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl,4-methyl-1-naphthyl, 4-methyl-1-anthryl, 4′-methylbiphenylyl,4″-t-butyl-p-terphenyl-4-yl and the like.

The substituted or non-substituted heteroaryloxy group having 5 to 50ring atoms is represented by —OZ′, and the examples of Z′ include2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl,4-pyridinyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl,7-indolyl, 1-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl,6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl,3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl,7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl,5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl,3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl,1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl,6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl,5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl,3-carbazolyl, 4-carbazolyl, 1-phenanthridinyl, 2-phenanthridinyl,3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl,7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl,10-phenanthryldinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl,9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl,1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl,1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl,1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl,1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl,1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl,1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl,1,8-phenanthroline-9-yl, 1,8-phenanthroline-10-yl,1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl,1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl,1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl,1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl,1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl,1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl,2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl,2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl,2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl,2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl,2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl,2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl,2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl,2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl,2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl,2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl,2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl,2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl,2-phenazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl,4-phenothiazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl,4-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl,5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl,2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl,3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl,3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl,3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl,2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl,4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl and thelike.

The substituted or non-substituted arylthio group having 6 to 50 ringcarbon atoms is represented by —SY″, and the examples of Y″ includephenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl,1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl,9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl,1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenylyl, 3-biphenylyl,4-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl,m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl,p-tolyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl,4-methyl-1-naphthyl, 4-methyl-1-anthryl, 4′-methylbiphenylyl,4″-t-butyl-p-terphenyl-4-yl and the like.

The substituted or non-substituted heteroarylthio group having 5 to 50ring atoms is represented by —SZ″, and the examples of Z″ include2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl,4-pyridinyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl,7-indolyl, 1-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl,6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl,3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl,7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl,5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl,3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl,1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl,6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl,5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl,3-carbazolyl, 4-carbazolyl, 1-phenanthridinyl, 2-phenanthridinyl,3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl,7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl,10-phenanthryldinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl,9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl,1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl,1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl,1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl,1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl,1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl,1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl,1,8-phenanthroline-9-yl, 1,8-phenanthroline-10-yl,1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl,1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl,1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl,1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl,1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl,1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl,2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl,2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl,2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl,2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl,2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl,2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl,2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl,2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl,2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl,2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl,2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl,2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl,2-phenazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl,4-phenothiazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl,4-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl,5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl,2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl,3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl,3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl,3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl,2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl,4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl and thelike.

The substituted or non-substituted alkoxycarbonyl group having 2 to 50carbon atoms is represented by —COOZ, and the examples of Z includemethyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl,n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl,2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl,1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl,chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl,1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl,1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl,2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl,2,3-dibromo-t-butyl, 1,2,3-tribromopropyl, iodomethyl, 1-iodoethyl,2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl,2,3-diiodo-t-butyl, 1,2,3-triiodopropyl, aminomethyl, 1-aminoethyl,2-aminoethyl, 2-aminoisobutyl, 1,2-diaminoethyl, 1,3-diaminoisopropyl,2,3-diamino-t-butyl, 1,2,3-triaminopropyl, cyanomethyl, 1-cyanoethyl,2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl,2,3-dicyano-t-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl,2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl,2,3-dinitro-t-butyl, 1,2,3-trinitropropyl and the like.

The amino group substituted with a substituted or non-substituted arylgroup having 6 to 50 ring carbon atoms or a substituted ornon-substituted heterocyclic group having 5 to 50 ring atoms isrepresented by —NPQ, and the examples of P and Q include phenyl,1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl,2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl,1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl, 1-pyrenyl, 2-pyrenyl,4-pyrenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, p-terphenyl-4-yl,p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl,m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-t-butylphenyl,p-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl,4-methyl-1-anthryl, 4′-methylbiphenylyl, 4″-t-butyl-p-terphenyl-4-yl,2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 3-pyridinyl,4-pyridinyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl,7-indolyl, 1-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl,6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl,3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl,7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl,5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl,3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl,1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl,6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl,5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl,3-carbazolyl, 4-carbazolyl, 1-phenanthridinyl, 2-phenanthridinyl,3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl,7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl,10-phenanthryldinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl,9-acridinyl, 1,7-phenanthroline-2-yl, 1,7-phenanthroline-3-yl,1,7-phenanthroline-4-yl, 1,7-phenanthroline-5-yl,1,7-phenanthroline-6-yl, 1,7-phenanthroline-8-yl,1,7-phenanthroline-9-yl, 1,7-phenanthroline-10-yl,1,8-phenanthroline-2-yl, 1,8-phenanthroline-3-yl,1,8-phenanthroline-4-yl, 1,8-phenanthroline-5-yl,1,8-phenanthroline-6-yl, 1,8-phenanthroline-7-yl,1,8-phenanthroline-9-yl, 1,8-phenanthroline-10-yl,1,9-phenanthroline-2-yl, 1,9-phenanthroline-3-yl,1,9-phenanthroline-4-yl, 1,9-phenanthroline-5-yl,1,9-phenanthroline-6-yl, 1,9-phenanthroline-7-yl,1,9-phenanthroline-8-yl, 1,9-phenanthroline-10-yl,1,10-phenanthroline-2-yl, 1,10-phenanthroline-3-yl,1,10-phenanthroline-4-yl, 1,10-phenanthroline-5-yl,2,9-phenanthroline-1-yl, 2,9-phenanthroline-3-yl,2,9-phenanthroline-4-yl, 2,9-phenanthroline-5-yl,2,9-phenanthroline-6-yl, 2,9-phenanthroline-7-yl,2,9-phenanthroline-8-yl, 2,9-phenanthroline-10-yl,2,8-phenanthroline-1-yl, 2,8-phenanthroline-3-yl,2,8-phenanthroline-4-yl, 2,8-phenanthroline-5-yl,2,8-phenanthroline-6-yl, 2,8-phenanthroline-7-yl,2,8-phenanthroline-9-yl, 2,8-phenanthroline-10-yl,2,7-phenanthroline-1-yl, 2,7-phenanthroline-3-yl,2,7-phenanthroline-4-yl, 2,7-phenanthroline-5-yl,2,7-phenanthroline-6-yl, 2,7-phenanthroline-8-yl,2,7-phenanthroline-9-yl, 2,7-phenanthroline-10-yl, 1-phenazinyl,2-phenazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl,4-phenothiazinyl, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl,4-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl,5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl,2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl,3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl,3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl,3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl,2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl,4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl and thelike.

The specific examples of the compound represented by Formula (I) shallbe shown below but shall not be restricted to them:

Further, an aromatic amine represented by Formula (II) shown below issuitably used as well for forming the hole injecting layer or the holetransporting layer:

In Formula (II), the definitions of Ar₁ to Ar₃ are the same as those ofAr¹ to Ar⁴ in Formula (I) described above. The specific examples of thecompound represented by Formula (II) shall be shown below but shall notbe restricted to them:

In the present invention, an anode of the organic EL device assumes arole of injecting holes into the hole transporting layer or the lightemitting layer and has effectively a work function of 4.5 eV or more.Indium tin oxide alloy (ITO), tin oxide (NESA), gold, silver, platinum,copper and the like can be applied as the specific examples of the anodematerial used in the present invention. Also, a material of the cathodehas preferably a small work function for the purpose of injectingelectrons into the electron injecting layer or the light emitting layer.The cathode material shall not specifically be restricted, and capableof being used are, to be specific, indium, aluminum, magnesium,magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithiumalloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and thelike.

The forming methods of the respective layers in the organic EL device ofthe present invention shall not specifically be restricted, and formingmethods carried out by a vacuum vapor deposition method, a spin coatingmethod and the like which have so far publicly been known can be used.The organic thin film layer containing the compound represented byFormula (1) described above which is used for the organic EL device ofthe present invention can be formed by a publicly known method carriedout by a vacuum vapor deposition method, a molecular beam evaporationmethod (MBE method) and a coating method such as a dipping method, aspin coating method, a casting method, a bar coating method and a rollcoating method each using a solution prepared by dissolving the compoundin a solvent.

The film thicknesses of the respective organic layers in the organic ELdevice of the present invention shall not specifically be restricted,and in general, if the film thicknesses are too small, defects such aspinholes and the like are liable to be caused. On the other hand, ifthey are too large, a high voltage has to be applied, and the efficiencyis deteriorated, so that they fall usually in a range of preferablyseveral nm to 1 μm.

EXAMPLES

Next, the present invention shall be explained in further details withreference to synthetic examples and examples, but the present inventionshall not be restricted to the synthetic examples and the examples shownbelow.

The evaluation methods of the organic EL device shall be describedbelow.

(1) External Quantum Efficiency (%):

The external quantum efficiency in a luminance of 1000 cd/m² wasmeasured at 23° C. under nitrogen gas atmosphere by means of a luminancemeter (spectroradiometer CS-1000, manufactured by Konica MinoltaSensing, Inc.).

(2) Half Life (Hour):

A continuous power supply test (direct current) was carried out at aninitial luminance of 1000 cd/m² to measure time passing until theinitial luminance was reduced by half.

(3) Voltage (V):

A voltage was applied to the electrically wired device under drynitrogen gas atmosphere by means of KEITHLY 236 SOURCE MEASURE UNIT toallow the device to emit light, and a voltage applied to wiringresistance other than the device was deducted to measure a voltageapplied to the device.

Synthetic Example 1 Synthesis of Compound (1) (1) Synthesis of Compound(1-a):

A three neck flask was charged with 40.1 g (240 mmol) of carbazole, 49.4g (200 mmol) of 2-bromodibenzofuran, 3.81 g (20 mmol) of copper iodide,84.91 g (400 mmol) of potassium phosphate, 7.21 ml (60 mmol) oftrans-1,2-diaminocyclohexane and 100 ml of 1,4-dioxane under nitrogenatmosphere, and the mixture was refluxed for 24 hours. After finishingthe reaction, the mixture was cooled down to room temperature and thendiluted with 400 ml of toluene. The inorganic salts and the like wereremoved by filtration under reduced pressure, and the filtrate waspassed through a short column of silica gel, and then concentrated. Itwas washed with an ethyl acetate/methanol mixed solvent to obtain awhite solid matter (compound (1-a)). Amount: 54.0 g and yield: 81%

(2) Synthesis of Compound (1-b):

A Kjeldahl flask was charged with 26.7 g (80 mmol) of the compound (1-a)and 160 ml of N,N-dimethylformamide under air to dissolve the sample,and the flask was cooled down to 0° C. on an ice and water bath. To asolution, N-bromosuccinimide 14.2 g (80 mmol) dissolved in 80 ml ofN,N-dimethylformamide was slowly dropwise added over a 10 minutes. Thesolution was stirred at 0° C. for 3 hours and then left standing at roomtemperature for a night. After finishing the reaction, 200 ml of toluenewas added thereto, and the solution was washed twice with water by meansof a separating funnel. It was dried on anhydrous magnesium sulfate andthen filtrated and concentrated. The concentrate was recrystallized fromhexane to obtain a white solid matter (compound (1-b)). Amount: 25.6 gand yield: 78%

(3) Synthesis of Compound (1-c):

A three neck flask was charged with 16.5 g (40 mmol) of the compound(1-b) and 200 ml of dehydrated tetrahydrofuran under nitrogen atmosphereto dissolve the sample, and the flask was cooled down to −78° C. To asolution, n-Butyllithium 30.6 ml (1.57M in hexane, 48 mmol) was dropwiseadded over 10 minutes. The solution was stirred at −78° C. for 20minutes, and then 18.3 ml (80 mmol) of triisopropyl borate was addedthereto in one lot, followed by stirring the solution at roomtemperature for 3 hours.

After finishing the reaction, the solution was concentrated to about ahalf, and 20 ml of a hydrochloric acid aqueous solution (1N) was addedthereto, followed by stirring the solution at room temperature for 2hours. The solution was extracted with dichloromethane by means of aseparating funnel, and the extract was dried on anhydrous magnesiumsulfate, filtrated and concentrated. The concentrate was purified bysilica gel chromatography (dichloromethane:ethyl acetate=9:1 as eluent),and then hexane was added thereto to precipitate a sample. The samplewas suspended and filtered off to give a white solid matter (compound(1-c)). Amount: 10.3 g and yield: 68%

(4) Synthesis of Compound (1):

A three neck flask was charged with 9.11 g (22.1 mmol) of the compound(1-b), 10.0 g (26.5 mmol) of the compound (1-c), 22.1 ml of a sodiumcarbonate 2M aqueous solution, 40 ml of 1,2-dimethoxyethane and 40 ml oftoluene, and 0.51 g (0.442 mmol) ofteterakis(triphenylphosphine)palladium was added to the above mixedsolution, followed by refluxing the solution for 8 hours.

After finishing the reaction, the solution was cooled down to roomtemperature, and then methanol was added thereto to recover aprecipitated sample and dry it under vacuum. The sample was dissolved in1 L of toluene by heating, and the solution was cooled down to roomtemperature. Then, it was allowed to pass through a short column ofsilica gel and concentrated. The concentrate was subjected to dispersewashing with ethyl acetate to obtain a white solid matter (compound(1)). Amount: 12.0 g and yield: 81%

Synthetic Example 2 Synthesis of Compound (3) (1) Synthesis of Compound(3-a):

A three neck flask was charged with 41.2 g (100 mmol) of the compound(1-b), 23.0 g (140 mmol) of mesityl boronic acid, 200 ml of a bariumhydroxide 2M aqueous solution and 50 ml of 1,2-dimethoxyethane undernitrogen atmosphere, and 3.47 g (3 mmol) ofteterakis(triphenylphosphine)palladium was added to the above mixedsolution, followed by refluxing the solution for 8 hours.

After finishing the reaction, the solution was cooled down to roomtemperature, and then the solution was extracted with toluene by meansof a separating funnel. The extract was dried on anhydrous magnesiumsulfate, filtrated and concentrated, and then the concentrate waspurified by silica gel chromatography (toluene:hexane=3:7). This wasrecrystallized from hexane to obtain a white solid matter (compound(3-a)). Amount: 15.3 g and yield: 34%

(2) Synthesis of Compound (3)

A compound (3) was synthesized by the same method as in the compounds(1-b) to (1), except that the raw material was changed from the compound(1-a) to the compound (3-a).

Synthetic Example 3 Synthesis of Compound (36)

A three neck flask was charged with 7.13 g (14.4 mmol) of the compound(3-c), 1.42 g (6 mmol) of 1,3-dibromobenzene, 12 ml of a sodiumcarbonate 2M aqueous solution, 12 ml of 1,2-dimethoxyethane and 12 ml oftoluene under nitrogen atmosphere, and 0.35 g (0.3 mmol) ofteterakis(triphenylphosphine)-palladium was added to the above mixedsolution, followed by refluxing the solution for 8 hours.

After finishing the reaction, the solution was cooled down to roomtemperature, and then the sample solution was transferred into aseparating funnel and extracted several times with toluene. The extractwas dried on anhydrous magnesium sulfate, then filtrated andconcentrated, and the concentrate was purified by silica gelchromatography to obtain a white solid matter (compound (36)). Amount:4.3 g and yield: 73%.

The above compounds were subjected to measurement of FD/MS andidentified by an agreement of the theoretical values of the molecularweights with the actual measured values thereof.

Comparative Synthetic Example Synthesis of Compound (33)

A three neck flask was charged with 5.43 g (14.4 mmol) of the compound(1-c), 1.42 g (6 mmol) of 1,3-dibromobenzene, 12 ml of a sodiumcarbonate 2M aqueous solution, 12 ml of 1,2-dimethoxyethane and 12 ml oftoluene under nitrogen atmosphere, and 0.35 g (0.3 mmol) ofteterakis(triphenylphosphine)-palladium was added to the above mixedsolution, followed by refluxing the solution for 8 hours.

After finishing the reaction, the solution was cooled down to roomtemperature, and then methanol was added thereto to recover apreicipitated sample and dry it under vacuum. The sample was dissolvedin 1 L of toluene by heating, and the solution was cooled down to roomtemperature. Then, it was allowed to pass through a short column ofsilica gel and concentrated. The concentrate was subjected to dispersewashing with a mixed solvent of ethyl acetate/hexane to obtain a whitesolid matter (compound (33)). Amount: 3.78 g and yield: 85%

Example 1

A glass substrate (manufactured by Geomatech Co., Ltd.) of 25 mm×75mm×1.1 mm equipped with an ITO transparent electrode was subjected tosonication in isopropyl alcohol for 5 minutes and then to UV ozonetreatment for 30 minutes. After the treatment, the glass substrateequipped with an ITO transparent electrode line was loaded in asubstrate holder of a vacuum vapor deposition apparatus, and a compound(HT) was subjected to resistance heating vapor deposition (thickness: 60nm) on a face of a side on which the transparent electrode line wasformed so that it covered the transparent electrode. The film-depositionrate was set to 1 Å/s. The above HT film functions as a holeinjecting-transporting layer.

Next, the compound (1) (host compound) was subjected to resistanceheating vapor deposition on the HT film to form a compound (1) filmhaving a thickness of 30 nm. Simultaneously, a compound (BD) as aphosphorescent dopant was deposited so that the compound (BD) accountedfor 10% in terms of a mass ratio based the compound (1). Thefilm-deposition rates were set to 1 Å/s and 0.11 Å/s respectively. Theabove film functions as a phosphorescent layer.

Next, a compound (HB) was subjected to resistance heating vapordeposition on the above phosphorescent emitting layer to form an HB filmhaving a thickness of 10 nm. The film-deposition rate was 1 Å/s. Theabove HB film functions as a hole blocking layer.

A tris(8-quinolinol)aluminum (Alq) complex was deposited (filmthickness: 30 nm) at a film-deposition rate of 1 Å/s on the above film.This film functions as an electron injecting layer.

Then, LiF was deposited (film thickness: 0.5 nm) at a film-depositionrate of 0.1 Å/s on the Alq film. Metal Al was deposited at afilm-deposition rate of 1 Å/s on the above LiF film to form a metalcathode (film thickness: 100 nm), and an organic EL device was obtained.

Examples 2 and 3

Organic EL devices were prepared in the same manner as in Example 1,except that host materials described in Table 1 were used in place ofthe compound (1) in Example 1.

Comparative Examples 1 to 6

Organic EL devices were prepared in the same manner as in Example 1,except that the following compounds (H1) to (H6) were used in place ofthe compound (1).

TABLE 1 Voltage External quantum Half life Host (V) efficiency (%)(hour) Example 1 (1) 7.4 6.3 1050 Example 2 (3) 7.6 11.1 1190 Example 3(36) 7.4 9.2 1010 Comparative Example 1 H1 8.8 7.0 700 ComparativeExample 2 H2 8.8 7.1 650 Comparative Example 3 H4 9.3 6.4 450Comparative Example 4 H5 9.5 6.9 480 Comparative Example 5 H6 9.3 6.9250 Comparative Example 6 (33) 8.3 7.2 1000

It can be found from the results shown in Table 1 that the compounds(1), (3) and (36) of the present invention have higher efficiencies andlonger lifetimes than those of the compounds used in ComparativeExamples 1 to 5. Further, it can be found that since the organic ELdevices of the present invention can be operated at lower voltages, theyare organic EL devices which are reduced in power consumption.

In Table 1, Comparative Example 6 is not comparable to the otherexamples in terms of a reduced voltage and a half life. This isconsidered to be due to that it is not comparable to the other examplesin terms of a chemical stability and control of a carrier balanceattributable to that all of 6-positions of carbazoles are hydrogen atomsand that they are not bonded at 3-positions via single bonds.

Example 4

A glass substrate (manufactured by Geomatech Co., Ltd.) of 25 mm×75mm×1.1 mm equipped with an ITO transparent electrode was subjected tosonication in isopropyl alcohol for 5 minutes and then to UV ozonetreatment for 30 minutes. After the treatment, the glass substrateequipped with an ITO transparent electrode line was loaded in asubstrate holder of a vacuum vapor deposition apparatus, and thecompound (1) was subjected to resistance heating vapor deposition(thickness: 60 nm) on a face of a side on which the transparentelectrode line was formed so that it covered the transparent electrode.The film-deposition rate was set to 1 Å/s. The above compound (1) filmfunctions as a hole injecting-transporting layer.

Next, a compound (A-1) (host compound) was subjected to resistanceheating vapor deposition on the compound (1) film to form a compound(A-1) film having a thickness of 30 nm. Simultaneously, the compound(BD) as a phosphorescent dopant was deposited so that the compound (BD)accounted for 10% in terms of a mass ratio based the compound (A-1). Thefilm-deposition rates were set to 1 Å/s and 0.11 Å/s respectively. Theabove film functions as a phosphorescent emitting layer.

Next, the compound (HB) (host compound) was subjected to resistanceheating vapor deposition on the above phosphorescent layer to form an HBfilm having a thickness of 10 nm. The film-deposition rate was 1 Å/s.The above HB film functions as a hole blocking layer.

A tris(8-quinolinol)aluminum (Alq) complex was deposited (filmthickness: 30 nm) on the above film. This film functions as an electroninjecting layer.

Then, LiF was deposited (film thickness: 0.5 nm) on the Alq film at afilm-deposition rate of 0.1 Å/s. Metal Al was deposited on the above LiFfilm at a film-forming rate of 1 Å/s to form a metal cathode (filmthickness: 100 nm), and an organic EL device was obtained.

Example 5

An organic EL device was prepared in the same manner as in Example 4,except that the compound (3) was used for the holeinjecting-transporting layer in place of the compound (1) in Example 4.

Comparative Example 7

An organic EL device was prepared in the same manner as in Example 4,except that the compound (HT) was used in place of the compound (1).

TABLE 2 Hole injecting- transporting Voltage External quantum Half lifelayer (V) efficiency (%) (hour) Example 4 (1) 8.3 10.4 1000 Example 5(3) 8.5 10.2 1030 Comparative HT 7.3 5.5 420 Example 7

It can be found from the results shown in Table 2 that the compounds (1)and (3) of the present invention have lower voltages, higherefficiencies and longer lifetimes than that of the compound used in thecomparative example.

INDUSTRIAL APPLICABILITY

As explained above in detail, use of the materials for an organic ELdevice according to the present invention provides organic EL deviceshaving a high light emission efficiency and a long lifetime.Accordingly, the organic EL devices of the present invention are veryuseful as displays for various electronic equipment, light sources andthe like.

1. A material for an organic electroluminescence device represented byFormula (1) shown below:

(in Formula (1), X¹ and X² each are independently an oxygen atom or asulfur atom, and they are not a sulfur atom at the same time; R¹ to R⁸each represent independently an alkyl group having 1 to 20 carbon atoms,a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy grouphaving 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 20 ringcarbon atoms, an aryl group having 6 to 18 ring carbon atoms, an aryloxygroup having 6 to 18 ring carbon atoms, a heteroaryl group having 5 to18 ring atoms, an amino group, a silyl group, a fluoro group or a cyanogroup, and the above substituents R¹ to R⁸ may be further substitutedwith the above substituents; when R¹ to R⁸ each are present in a pluralnumber, they may be the same as or different from each other; a, d, fand h each represent independently an integer of any of 0 to 4, and b,c, e and g each represent independently an integer of any of 0 to 3; asum of a to h is 6 or less; L¹ represents a single bond, a divalentlinkage group containing N, a divalent linkage group containing 0, adivalent linkage group containing Si, a divalent linkage groupcontaining P, a divalent linkage group containing S, an alkylene grouphaving 1 to 20 carbon atoms, a cycloalkylene group having 3 to 20 ringcarbon atoms, an arylene group having 6 to 18 ring carbon atoms, aheteroarylene group having 5 to 18 ring atoms, a divalent amino group ora divalent silyl group; L² and L³ each represent independently a singlebond, an alkylene group having 1 to 20 carbon atoms, a cycloalkylenegroup having 3 to 20 ring carbon atoms, an arylene group having 6 to 18ring carbon atoms or a heteroarylene group having 5 to 18 ring atoms; L¹to L³ may be further substituted with any of the substituents R¹ to R⁸described above; provided that when L¹ is an arylene group having 6 to18 ring carbon atoms or a heteroarylene group having 5 to 18 ring atoms,a and d each represent independently an integer of any of 1 to 4).
 2. Amaterial for an organic electroluminescence device represented byFormula (2) shown below:

(in Formula (2), X¹ and X², R¹ to R⁸, a to h and L¹ to L³ are the sameas described above).
 3. The material for an organic electroluminescencedevice according to claim 1 or 2, wherein L² and L³ are single bonds. 4.The material for an organic electroluminescence device according to anyof claims 1 to 3, represented by the following Formula (3):

(in Formula (3), R^(1a), R^(4a), R^(6a) and R^(8a) each representindependently a hydrogen atom or an aryl group having 6 to 18 ringcarbon atoms, and the above aryl group may be further substituted withthe substituent R described above; and X¹, X² and L¹ to L³ are the sameas described above).
 5. The material for an organic electroluminescencedevice according to any of claims 1 to 4, wherein L¹ is a single bond.6. An organic electroluminescence device provided with one or moreorganic thin film layers including a light emitting layer between acathode and an anode, wherein at least one layer of the above organicthin film layers contains the material for an organicelectroluminescence device according to any of claims 1 to
 5. 7. Theorganic electroluminescence device according to claim 6, wherein thelight emitting layer contains the material for an organicelectroluminescence device described above as a host material.
 8. Theorganic electroluminescence device according to claim 6, wherein thelight emitting layer contains a host material and a phosphorescenceluminescence material, and the above host material is the material foran organic electroluminescence device described above.
 9. The organicelectroluminescence device according to claim 8, wherein thephosphorescence luminescence material is a compound containing metalselected from iridium (Ir), osmium (Os) and platinum (Pt).
 10. Theorganic electroluminescence device according to claim 9, wherein thecompound containing metal is an ortho-metallization metal complex. 11.The organic electroluminescence device according to any of claims 6 to10, wherein a reducing dopant is contained in an interfacial regionbetween the cathode and the organic thin film layer.
 12. The organicelectroluminescence device according to any of claims 6 to 10, whereinan electron injecting layer is provided between the light emitting layerand the cathode, and the above electron injecting layer contains anitrogen-containing heterocyclic derivative.
 13. The organicelectroluminescence device according to any of claims 6 to 10, wherein ahole transporting layer is provided between the light emitting layer andthe anode, and the above hole transporting layer contains the materialfor an organic electroluminescence device described above.